Climate changes and urban population growth are increasing the heat island effects in cities, making the urban outdoor environment less comfortable for people. Consequently, improving the thermal comfort conditions of urban open spaces could be considered one important challenge that cities can pursue in the upcoming years. As a first step, this work aims to assess which GIS tools are most useful for evaluating place-based outdoor thermal comfort conditions at urban scale. The UMEP-SOLWEIG (QGIS) tool was described and compared with ENVI-met, to calculate the thermal comfort indexes in different outdoor spaces, during extreme summer and winter conditions, in the city of Turin. These tools can be easily implemented in platforms to represent the spatial distribution of thermal comfort conditions in cities for prioritizing strategies and defining effective actions within land-use plans. This type of representation is crucial as it provides very comprehensible results to urban or regional planners and policy-makers. In this study, UMEP-SOLWEIG appeared to be the most suitable tool since it is the best compromise between simulation time and accuracy at urban scale.